2,4,5-tris(4-bromophenyl)-1-methyl-1H-imidazole | 1360596-78-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,4,5-tris(4-bromophenyl)-1-methyl-1H-imidazole
• 英文别名: 2,4,5-Tris(4-bromophenyl)-1-methylimidazole；2,4,5-tris(4-bromophenyl)-1-methylimidazole
• CAS: 1360596-78-6
• 化学式: C₂₂H₁₅Br₃N₂
• 分子量: 547.087
• InChiKey: TVQBKPYZIIJPKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,4,5-tris(4-bromophenyl)imidazole 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 以90.3%的产率得到2,4,5-tris(4-bromophenyl)-1-methyl-1H-imidazole
  参考文献：
  名称：

  钯纳米粒子修饰的芳基碘化物氰化多孔有机聚（三苯基咪唑）

  摘要：

  通过2,4,5-三（4-溴苯基）-1-甲基-1 H-咪唑（TPI-Me）的Yamamoto自偶联反应制备了一种新型的多孔有机聚（三苯基咪唑）PTPI-Me。在存在双（1,5-环辛二烯）镍（0）的情况下。随后用Pd纳米颗粒（NPs）修饰聚合物，以提供异质氰化催化剂Pd @ PTPI-Me。由于咪唑环与Pd的配位作用，平均直径2.7 nm的Pd NPs在PTPI-Me框架内生长。所得Pd @ PTPI-Me催化剂的Pd负载量为0.13 mmol g -1，对芳基碘化物的氰化反应表现出优异的催化活性。更重要的是，非均相催化剂也易于循环使用，并在五个循环后表现出可忽略不计的失活。

  DOI：

  10.1002/asia.201800681

文献信息

• Novel Triarylimidazole Redox Catalysts: Synthesis, Electrochemical Properties, and Applicability to Electrooxidative C–H Activation
  作者：Cheng-chu Zeng、Ni-tao Zhang、Chiu Marco Lam、R. Daniel Little

  DOI：10.1021/ol300195c

  日期：2012.3.2

  A new class of metal-free, easy to synthesize redox catalysts based on a triarylimidazole framework is described. With those synthesized thus far, one can access a potential range of ca. 410 mV. They proved to be useful mediators for the activation of benzylic C-H bonds under mild conditions.
• Triarylimidazole Redox Catalysts: Electrochemical Analysis and Empirical Correlations
  作者：Ni-tao Zhang、Cheng-chu Zeng、Chiu Marco Lam、Randi K. Gbur、R. Daniel Little

  DOI：10.1021/jo302309m

  日期：2013.3.1

  A series of triarylimidazoles was synthesized and characterized electrochemically. The synthetic route is general, providing a pathway to 30 redox mediators that exhibit a > 700 mV range of accessible potentials. Most of the triarylimidazoles display three oxidation peaks where the first redox couple is quasi-reversible. The electronic character of the substituents affects the oxidation potential. This is exemplified by a linear correlation between the first oxidation potential and the sum of the Hammett sigma(+) substituent constants, as well as with a series of calculated ionization potentials. We close by putting forward a rule of thumb stating that for a given mediator, the upper limit of accessible potentials can be extended by at least 500 mV beyond the largest recorded value. A rationale, the conditions under which the rule is likely to apply, and an example are provided.